Stereocontrolled Total Synthesis of (-)-Isocelorbicol and Its Elaboration to Natural Dihydro-β-agarofuran Esters

Tomoyo Mohri; Yusuke Takahashi; Eunsang Kwon; Shigefumi Kuwahara; Yusuke Ogura

doi:10.1021/acs.orglett.0c03419

Stereocontrolled Total Synthesis of (-)-Isocelorbicol and Its Elaboration to Natural Dihydro-β-agarofuran Esters

Tomoyo Mohri, Yusuke Takahashi, Eunsang Kwon, Shigefumi Kuwahara, Yusuke Ogura

SCI - Research and Analytical Center for Giant Molecules

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

The first total synthesis of four naturally occurring dihydro-β-agarofuran esters has been accomplished via a highly stereocontrolled 14-step access to their common core triol, (-)-isocelorbicol. A semipinacol rearrangement of an epoxy alcohol to install a quaternary carbon, diastereoselective conjugate reduction of a spirocyclic butenolide for the establishment of a methyl-bearing chiral center, and ring-closing metathesis to construct the decalin ring system were exploited as the key steps for the high-yielding synthesis of (-)-isocelorbicol.

Original language	English
Pages (from-to)	9234-9238
Number of pages	5
Journal	Organic letters
Volume	22
Issue number	23
DOIs	https://doi.org/10.1021/acs.orglett.0c03419
Publication status	Published - 2020 Dec 4

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c03419

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title = "Stereocontrolled Total Synthesis of (-)-Isocelorbicol and Its Elaboration to Natural Dihydro-β-agarofuran Esters",

abstract = "The first total synthesis of four naturally occurring dihydro-β-agarofuran esters has been accomplished via a highly stereocontrolled 14-step access to their common core triol, (-)-isocelorbicol. A semipinacol rearrangement of an epoxy alcohol to install a quaternary carbon, diastereoselective conjugate reduction of a spirocyclic butenolide for the establishment of a methyl-bearing chiral center, and ring-closing metathesis to construct the decalin ring system were exploited as the key steps for the high-yielding synthesis of (-)-isocelorbicol. ",

author = "Tomoyo Mohri and Yusuke Takahashi and Eunsang Kwon and Shigefumi Kuwahara and Yusuke Ogura",

note = "Funding Information: This work was financially supported by the Kato Memorial Bioscience Foundation. We thank Ms. Yuka Taguchi (Tohoku University) for her help with MS and NMR measurements. Publisher Copyright: {\textcopyright} 2020 American Chemical Society",

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AU - Mohri, Tomoyo

AU - Takahashi, Yusuke

AU - Kwon, Eunsang

AU - Kuwahara, Shigefumi

AU - Ogura, Yusuke

N1 - Funding Information: This work was financially supported by the Kato Memorial Bioscience Foundation. We thank Ms. Yuka Taguchi (Tohoku University) for her help with MS and NMR measurements. Publisher Copyright: © 2020 American Chemical Society

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Stereocontrolled Total Synthesis of (-)-Isocelorbicol and Its Elaboration to Natural Dihydro-β-agarofuran Esters

Abstract

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